US3663728A - Process for producing polyamide acid and polyimides - Google Patents
Process for producing polyamide acid and polyimides Download PDFInfo
- Publication number
- US3663728A US3663728A US747460A US3663728DA US3663728A US 3663728 A US3663728 A US 3663728A US 747460 A US747460 A US 747460A US 3663728D A US3663728D A US 3663728DA US 3663728 A US3663728 A US 3663728A
- Authority
- US
- United States
- Prior art keywords
- grams
- diamine
- polyamide acid
- dianhydride
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004952 Polyamide Substances 0.000 title abstract description 38
- 239000002253 acid Substances 0.000 title abstract description 38
- 229920002647 polyamide Polymers 0.000 title abstract description 38
- 229920001721 polyimide Polymers 0.000 title abstract description 14
- 239000004642 Polyimide Substances 0.000 title abstract description 11
- 238000000034 method Methods 0.000 title description 36
- 150000004985 diamines Chemical class 0.000 abstract description 30
- 239000002904 solvent Substances 0.000 abstract description 27
- 229920005862 polyol Polymers 0.000 abstract description 16
- 238000009413 insulation Methods 0.000 abstract description 5
- 150000003077 polyols Chemical class 0.000 abstract description 5
- 239000002966 varnish Substances 0.000 abstract description 5
- 238000007598 dipping method Methods 0.000 abstract description 3
- 239000009719 polyimide resin Substances 0.000 abstract description 3
- 238000010030 laminating Methods 0.000 abstract description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 61
- 239000000243 solution Substances 0.000 description 43
- -1 aliphatic polyol Chemical class 0.000 description 27
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000012456 homogeneous solution Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 125000006159 dianhydride group Chemical group 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- OSGFBINRYVUILV-UHFFFAOYSA-N 4-[(4-aminophenyl)-diethylsilyl]aniline Chemical compound C=1C=C(N)C=CC=1[Si](CC)(CC)C1=CC=C(N)C=C1 OSGFBINRYVUILV-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- RLFFWWKJSJOYMQ-UHFFFAOYSA-N 1,3-diazepan-2-one Chemical compound O=C1NCCCCN1 RLFFWWKJSJOYMQ-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- YLHUPYSUKYAIBW-UHFFFAOYSA-N 1-acetylpyrrolidin-2-one Chemical compound CC(=O)N1CCCC1=O YLHUPYSUKYAIBW-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- 125000004825 2,2-dimethylpropylene group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[*:1])C([H])([H])[*:2] 0.000 description 1
- IUYHQGMDSZOPDZ-UHFFFAOYSA-N 2,3,4-trichlorobiphenyl Chemical group ClC1=C(Cl)C(Cl)=CC=C1C1=CC=CC=C1 IUYHQGMDSZOPDZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- POTQBGGWSWSMCX-UHFFFAOYSA-N 3-[2-(3-aminopropoxy)ethoxy]propan-1-amine Chemical compound NCCCOCCOCCCN POTQBGGWSWSMCX-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- DRBYXWVRZYMIEO-UHFFFAOYSA-N 4-[methyl(trimethylsilyloxy)silyl]butan-1-amine Chemical compound NCCCC[SiH](O[Si](C)(C)C)C DRBYXWVRZYMIEO-UHFFFAOYSA-N 0.000 description 1
- OCMRIRBBPSOFIL-UHFFFAOYSA-N 6,6-dimethyl-4-phenylcyclohexa-2,4-diene-1,1-diamine Chemical group C1=CC(N)(N)C(C)(C)C=C1C1=CC=CC=C1 OCMRIRBBPSOFIL-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 239000006061 abrasive grain Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- CBLAIDIBZHTGLV-UHFFFAOYSA-N dodecane-2,11-diamine Chemical compound CC(N)CCCCCCCCC(C)N CBLAIDIBZHTGLV-UHFFFAOYSA-N 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- RESSOZOGQXKCKT-UHFFFAOYSA-N ethene;propane-1,2-diol Chemical class C=C.CC(O)CO RESSOZOGQXKCKT-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- VQXBKCWOCJSIRT-UHFFFAOYSA-N octadecane-1,12-diamine Chemical compound CCCCCCC(N)CCCCCCCCCCCN VQXBKCWOCJSIRT-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 125000006160 pyromellitic dianhydride group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
- C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
- C09D5/4419—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
- C09D5/4461—Polyamides; Polyimides
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74746068A | 1968-07-25 | 1968-07-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3663728A true US3663728A (en) | 1972-05-16 |
Family
ID=25005152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US747460A Expired - Lifetime US3663728A (en) | 1968-07-25 | 1968-07-25 | Process for producing polyamide acid and polyimides |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3663728A (de) |
| DE (1) | DE1937388A1 (de) |
| FR (1) | FR2013718A1 (de) |
| GB (1) | GB1224445A (de) |
Cited By (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3850773A (en) * | 1972-06-23 | 1974-11-26 | Gen Electric | Method for making polyimide coated conductors in a continuous manner |
| US3892647A (en) * | 1970-03-12 | 1975-07-01 | Gen Electric | Method of electrodepositing a polymer |
| US3903046A (en) * | 1972-02-24 | 1975-09-02 | Ciba Geigy Corp | Process for the production of shapeable polymers containing N-silyl groups |
| US3902981A (en) * | 1971-05-11 | 1975-09-02 | Du Pont | Process for electrophoretic deposition |
| US3925313A (en) * | 1973-11-09 | 1975-12-09 | Nitto Electric Ind Co | Polyimide water-soluble composition |
| US3980601A (en) * | 1972-03-04 | 1976-09-14 | Badische Anilin- & Soda-Fabrik Aktiengesellschaft | Thermostable coating, impregnating and bonding agents |
| US4011361A (en) * | 1975-06-18 | 1977-03-08 | E. I. Du Pont De Nemours And Company | Fluoropolymer coating compositions having improved adhesion |
| US4014832A (en) * | 1974-05-01 | 1977-03-29 | Nitto Electric Industrial Co., Ltd. | Heat resistant resin solution and method for preparation thereof |
| US4014834A (en) * | 1975-02-04 | 1977-03-29 | E. I. Du Pont De Nemours And Company | Aqueous solutions of polyamide acids which can be precursors of polyimide polymers |
| US4016125A (en) * | 1975-07-21 | 1977-04-05 | E. I. Du Pont De Nemours And Co. | Fluoropolymer coating compositions having improved adhesion |
| US4039713A (en) * | 1975-07-31 | 1977-08-02 | E. I. Du Pont De Nemours And Company | Fluorocarbon primer having improved scratch resistance |
| US4045407A (en) * | 1976-02-23 | 1977-08-30 | Standard Oil Company (Indiana) | Process for preparing amideimide polymers in the presence of alcoholic solvent |
| US4049863A (en) * | 1975-07-31 | 1977-09-20 | E. I. Du Pont De Nemours And Company | Fluoropolymer primer having improved scratch resistance |
| US4053444A (en) * | 1972-04-19 | 1977-10-11 | Westinghouse Electric Corporation | Colloidal polyamic acid electrodeposition compositions and process for preparing said compositions |
| US4107355A (en) * | 1976-03-25 | 1978-08-15 | Dr. Kurt Herberts & Co. Gesellschaft Mit Mit Beschrankter Haftung Vorm. Otto Louis Becker | Process for the production of highly heat-resistant insulating coatings on electrical conductors |
| US4115341A (en) * | 1977-01-24 | 1978-09-19 | General Electric Company | Polyetheramide-acid-imide solution and process for preparation thereof |
| US4157996A (en) * | 1977-03-18 | 1979-06-12 | General Electric Company | Coating solution of polyetherimide-forming monomers |
| US4180612A (en) * | 1974-03-04 | 1979-12-25 | General Electric Company | Hydantoin-polyester coating compositions |
| US4181641A (en) * | 1977-01-24 | 1980-01-01 | General Electric Company | Polyetheramide-acid-imide solution and process for preparation thereof |
| US4334973A (en) * | 1980-07-18 | 1982-06-15 | Westinghouse Electric Corp. | Process for electrophoretically forming an imide coating on wire |
| US4428977A (en) | 1969-05-08 | 1984-01-31 | General Electric Company | Ammonium salt of partially emidized polyamide acid for aqueous coating composition |
| US5061783A (en) * | 1987-04-07 | 1991-10-29 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Processing for maximizing the level of crystallinity in linear aromatic polyimides |
| EP0455571A2 (de) * | 1990-03-30 | 1991-11-06 | International Business Machines Corporation | Niedrig-Wärmeausdehnungskoeffiziente (TCE)-Polyimide |
| US6432348B1 (en) * | 1998-06-29 | 2002-08-13 | Sony Corporation | Process for forming polyimide composite electro-deposited film |
| US20140213724A1 (en) * | 2013-01-31 | 2014-07-31 | Fuji Xerox Co., Ltd. | Polyimide precursor composition and method for producing polyimide precursor composition |
| US20150232619A1 (en) * | 2014-02-18 | 2015-08-20 | Tokyo Ohka Kogyo Co., Ltd. | Method of producing polyimide resin, method of producing polyimide coating, method of producing polyamic acid solution, polyimide coating, and polyamic acid solution |
| US9505886B2 (en) | 2014-07-25 | 2016-11-29 | Fuji Xerox Co., Ltd. | Polyimide precursor composition, method for preparing polyimide precursor, polyimide molded article, and method for preparing polyimide molded article |
| US9550862B2 (en) | 2014-07-25 | 2017-01-24 | Fuji Xerox Co., Ltd. | Polyimide precursor composition, method for preparing polyimide precursor, polyimide molded article, and method for preparing polyimide molded article |
| US20190071569A1 (en) * | 2017-09-01 | 2019-03-07 | Fuji Xerox Co., Ltd. | Polyimide precursor solution and polyimide shaped article |
| CN114805806A (zh) * | 2022-05-10 | 2022-07-29 | 上海华谊三爱富新材料有限公司 | 降低聚酰胺酸溶液粘度的方法和聚酰亚胺膜的制备方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2111640A1 (de) * | 1970-03-12 | 1971-09-30 | Gen Electric | Verfahren zur Herstellung von elektrophoretisch abscheidbaren UEberzugsmassen |
| DE4135056A1 (de) * | 1991-10-24 | 1993-04-29 | Basf Lacke & Farben | Loesungen von polyimidbildenden ausgangsstoffen |
-
1968
- 1968-07-25 US US747460A patent/US3663728A/en not_active Expired - Lifetime
-
1969
- 1969-05-09 GB GB23793/69A patent/GB1224445A/en not_active Expired
- 1969-07-23 DE DE19691937388 patent/DE1937388A1/de active Pending
- 1969-07-25 FR FR6925604A patent/FR2013718A1/fr not_active Withdrawn
Cited By (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4428977A (en) | 1969-05-08 | 1984-01-31 | General Electric Company | Ammonium salt of partially emidized polyamide acid for aqueous coating composition |
| US3892647A (en) * | 1970-03-12 | 1975-07-01 | Gen Electric | Method of electrodepositing a polymer |
| US3902981A (en) * | 1971-05-11 | 1975-09-02 | Du Pont | Process for electrophoretic deposition |
| US3903046A (en) * | 1972-02-24 | 1975-09-02 | Ciba Geigy Corp | Process for the production of shapeable polymers containing N-silyl groups |
| US3980601A (en) * | 1972-03-04 | 1976-09-14 | Badische Anilin- & Soda-Fabrik Aktiengesellschaft | Thermostable coating, impregnating and bonding agents |
| US4053444A (en) * | 1972-04-19 | 1977-10-11 | Westinghouse Electric Corporation | Colloidal polyamic acid electrodeposition compositions and process for preparing said compositions |
| US3850773A (en) * | 1972-06-23 | 1974-11-26 | Gen Electric | Method for making polyimide coated conductors in a continuous manner |
| US3925313A (en) * | 1973-11-09 | 1975-12-09 | Nitto Electric Ind Co | Polyimide water-soluble composition |
| US4180612A (en) * | 1974-03-04 | 1979-12-25 | General Electric Company | Hydantoin-polyester coating compositions |
| US4014832A (en) * | 1974-05-01 | 1977-03-29 | Nitto Electric Industrial Co., Ltd. | Heat resistant resin solution and method for preparation thereof |
| US4014834A (en) * | 1975-02-04 | 1977-03-29 | E. I. Du Pont De Nemours And Company | Aqueous solutions of polyamide acids which can be precursors of polyimide polymers |
| US4011361A (en) * | 1975-06-18 | 1977-03-08 | E. I. Du Pont De Nemours And Company | Fluoropolymer coating compositions having improved adhesion |
| US4070525A (en) * | 1975-07-21 | 1978-01-24 | E. I. Du Pont De Nemours And Company | Fluoropolymer coating compositions having improved adhesion |
| US4016125A (en) * | 1975-07-21 | 1977-04-05 | E. I. Du Pont De Nemours And Co. | Fluoropolymer coating compositions having improved adhesion |
| US4049863A (en) * | 1975-07-31 | 1977-09-20 | E. I. Du Pont De Nemours And Company | Fluoropolymer primer having improved scratch resistance |
| US4039713A (en) * | 1975-07-31 | 1977-08-02 | E. I. Du Pont De Nemours And Company | Fluorocarbon primer having improved scratch resistance |
| US4045407A (en) * | 1976-02-23 | 1977-08-30 | Standard Oil Company (Indiana) | Process for preparing amideimide polymers in the presence of alcoholic solvent |
| US4107355A (en) * | 1976-03-25 | 1978-08-15 | Dr. Kurt Herberts & Co. Gesellschaft Mit Mit Beschrankter Haftung Vorm. Otto Louis Becker | Process for the production of highly heat-resistant insulating coatings on electrical conductors |
| US4115341A (en) * | 1977-01-24 | 1978-09-19 | General Electric Company | Polyetheramide-acid-imide solution and process for preparation thereof |
| US4181641A (en) * | 1977-01-24 | 1980-01-01 | General Electric Company | Polyetheramide-acid-imide solution and process for preparation thereof |
| US4157996A (en) * | 1977-03-18 | 1979-06-12 | General Electric Company | Coating solution of polyetherimide-forming monomers |
| US4334973A (en) * | 1980-07-18 | 1982-06-15 | Westinghouse Electric Corp. | Process for electrophoretically forming an imide coating on wire |
| US5061783A (en) * | 1987-04-07 | 1991-10-29 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Processing for maximizing the level of crystallinity in linear aromatic polyimides |
| EP0455571A2 (de) * | 1990-03-30 | 1991-11-06 | International Business Machines Corporation | Niedrig-Wärmeausdehnungskoeffiziente (TCE)-Polyimide |
| EP0455571A3 (en) * | 1990-03-30 | 1992-01-22 | International Business Machines Corporation | Low thermal coefficients of expansion(tce) polyimides |
| US6432348B1 (en) * | 1998-06-29 | 2002-08-13 | Sony Corporation | Process for forming polyimide composite electro-deposited film |
| US20140213724A1 (en) * | 2013-01-31 | 2014-07-31 | Fuji Xerox Co., Ltd. | Polyimide precursor composition and method for producing polyimide precursor composition |
| US20150232619A1 (en) * | 2014-02-18 | 2015-08-20 | Tokyo Ohka Kogyo Co., Ltd. | Method of producing polyimide resin, method of producing polyimide coating, method of producing polyamic acid solution, polyimide coating, and polyamic acid solution |
| US10208163B2 (en) * | 2014-02-18 | 2019-02-19 | Tokyo Ohka Kogyo Co., Ltd. | Method of producing polyimide resin, method of producing polyimide coating, method of producing polyamic acid solution, polyimide coating, and polyamic acid solution |
| US9505886B2 (en) | 2014-07-25 | 2016-11-29 | Fuji Xerox Co., Ltd. | Polyimide precursor composition, method for preparing polyimide precursor, polyimide molded article, and method for preparing polyimide molded article |
| US9550862B2 (en) | 2014-07-25 | 2017-01-24 | Fuji Xerox Co., Ltd. | Polyimide precursor composition, method for preparing polyimide precursor, polyimide molded article, and method for preparing polyimide molded article |
| US20190071569A1 (en) * | 2017-09-01 | 2019-03-07 | Fuji Xerox Co., Ltd. | Polyimide precursor solution and polyimide shaped article |
| US11339289B2 (en) * | 2017-09-01 | 2022-05-24 | Fujifilm Business Innovation Corp. | Polyimide precursor solution and polyimide shaped article |
| CN114805806A (zh) * | 2022-05-10 | 2022-07-29 | 上海华谊三爱富新材料有限公司 | 降低聚酰胺酸溶液粘度的方法和聚酰亚胺膜的制备方法 |
| CN114805806B (zh) * | 2022-05-10 | 2024-04-02 | 上海华谊三爱富新材料有限公司 | 降低聚酰胺酸溶液粘度的方法和聚酰亚胺膜的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1937388A1 (de) | 1970-01-29 |
| FR2013718A1 (de) | 1970-04-03 |
| GB1224445A (en) | 1971-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: INSULATING MATERIALS INCORPORATED, ONE CAMPBELL RD Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:GENERAL ELECTRIC COMPANY;REEL/FRAME:005500/0044 Effective date: 19880524 |
|
| AS | Assignment |
Owner name: CHEMICAL BANK,NEW YORK Free format text: SECURITY INTEREST;ASSIGNOR:INSULATING MATERIALS INCORPORATED;REEL/FRAME:004886/0633 Effective date: 19880318 Owner name: CHEMICAL BANK, 41 STATE STREET, ALBANY, NEW YORK 1 Free format text: SECURITY INTEREST;ASSIGNOR:INSULATING MATERIALS INCORPORATED;REEL/FRAME:004886/0633 Effective date: 19880318 |